US10392462B2 - Photosensitive composition containing oxime-ester photoinitiator and application thereof - Google Patents

Photosensitive composition containing oxime-ester photoinitiator and application thereof Download PDF

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US10392462B2
US10392462B2 US15/324,996 US201515324996A US10392462B2 US 10392462 B2 US10392462 B2 US 10392462B2 US 201515324996 A US201515324996 A US 201515324996A US 10392462 B2 US10392462 B2 US 10392462B2
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photosensitive composition
meth
acrylate
oxime ester
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US20170210838A1 (en
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Xiaochun Qian
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Changzhou Tronly New Electronic Materials Co Ltd
Changzhou Tronly Advanced Electronic Materials Co Ltd
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Changzhou Tronly New Electronic Materials Co Ltd
Changzhou Tronly Advanced Electronic Materials Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
    • C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
    • C08F265/06—Polymerisation of acrylate or methacrylate esters on to polymers thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
    • C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
    • C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/10—Esters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
    • C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
    • C09D4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/22—Absorbing filters
    • G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
    • G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
    • G03F7/031—Organic compounds not covered by group G03F7/029
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
    • G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/16—Coating processes; Apparatus therefor
    • G03F7/162—Coating on a rotating support, e.g. using a whirler or a spinner
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/16—Coating processes; Apparatus therefor
    • G03F7/168—Finishing the coated layer, e.g. drying, baking, soaking
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/20—Exposure; Apparatus therefor
    • G03F7/2002—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image
    • G03F7/2004—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image characterised by the use of a particular light source, e.g. fluorescent lamps or deep UV light
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/26—Processing photosensitive materials; Apparatus therefor
    • G03F7/30—Imagewise removal using liquid means
    • G03F7/32—Liquid compositions therefor, e.g. developers
    • G03F7/322—Aqueous alkaline compositions
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/26—Processing photosensitive materials; Apparatus therefor
    • G03F7/38—Treatment before imagewise removal, e.g. prebaking
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/04—Acids; Metal salts or ammonium salts thereof
    • C08F220/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/20—Esters of polyhydric alcohols or phenols, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate
    • C08F2220/185—

Definitions

  • This invention belongs to the technical field of photocuring, and particularly to a photosensitive composition (i.e., a photocurable composition) containing an oxime ester photoinitiator and application thereof in a liquid crystal display apparatus, such as a color filter, a photospacer, or a rib.
  • a photosensitive composition i.e., a photocurable composition
  • a liquid crystal display apparatus such as a color filter, a photospacer, or a rib.
  • oxime ester photoinitiators have been gradually used in photosensitive compositions due to relatively excellent photosensitive property thereof.
  • the photosensitivity, the developability, and the resolution effect are not good, and not only the production efficiency is reduced, but also the resultant products cannot achieve required precision and reliability.
  • an object of this invention is to provide a photosensitive composition containing an oxime ester photoinitiator, which contains a compound of formula (I) as a photoinitiator and monomers and polymers adapted to the photoinitiator.
  • This composition has the advantages of high curing speed, small exposure dose, low pollution, low energy consumption, few deficiencies of residues, etc. It is experimentally demonstrated that the thickness, the clarity, and the pattern integrity of the film formed thereby are all greatly superior to those of products of the same type.
  • a photosensitive composition containing an oxime ester photoinitiator comprising the following components:
  • the oxime ester photoinitiator as component (C) being at least one selected from the group consisting of bisoxime ester compounds represented by the following general formula (I):
  • A is blank (i.e., two benzene rings on the left and on the right are connected with each other only by B), a single bond, or a C 1 -C 5 alkylene group
  • B is O, S, or a R 5 N— group, wherein R 5 is hydrogen, a C 1 -C 20 linear or branched alkyl group, a C 3 -C 20 cycloalkyl group, a C 4 -C 20 cycloalkylalkyl group, or a C 4 -C 20 alkylcycloalkyl group;
  • R 6 and R 7 each independently represent hydrogen, halogen, a nitro group, a hydroxy group, a carboxyl group, a sulfonic acid group, an amino group, a cyano group, or an alkoxy group, or a C 1 -C 20 linear or branched alkyl group, a C 3 -C 20 cycloalkyl group, a C 4 -
  • X and Y each independently represent a carbonyl (—CO—) or a single bond
  • R 2 and R 3 each independently represent hydrogen, a C 1 -C 20 linear or branched alkyl group, a C 3 -C 20 cycloalkyl group, a C 4 -C 20 cycloalkylalkyl group, a C 4 -C 20 alkylcycloalkyl group, or a C 7 -C 20 aralkyl group, and optionally, one or more hydrogens in the above groups may be each independently substituted with a group selected from the group consisting of halogen, a nitro group, a hydroxy group, a carboxyl group, a sulfonic acid group, an amino group, a cyano group, and an alkoxy group;
  • R 4 independently represents a C 1 -C 20 linear or branched alkyl group, a C 3 -C 20 cycloalkyl group, a C 4 -C 20 cycloalkylalkyl group, a C 4 -C 20 alkylcycloalkyl group, a C 3 -C 20 heteroaryl group, or a C 6 -C 20 aryl group, and optionally, one or more hydrogens in the above groups may be each independently substituted with a group selected from the group consisting of halogen, a phenyl group, a nitro group, a hydroxy group, a carboxyl group, a sulfonic acid group, an amino group, a cyano group, and an alkoxy group.
  • the oxime ester photoinitiator as component (C) may be prepared by the following method:
  • the oxime compound being reacted with the acid anhydride or the acid chloride to obtain the oxime ester photoinitiator.
  • the oxime ester photoinitiator as component (C) is one or a combination of two or more selected from the following structures:
  • the ultraviolet photosensitive prepolymer resin as component (A) is not particularly limited, and a well-known conventional ultraviolet photosensitive prepolymer resin can be used.
  • resins having a vinyl unsaturated group are preferred, and more preferably, they are used in combination.
  • the active diluent monomer as component (B) is not particularly limited, and a well-known conventional active diluent monomer can be used.
  • monomers having a vinyl unsaturated group are preferred, and more preferably, they are used in combination.
  • the monomers having a vinyl unsaturated group include monofunctional monomers and polyfuctional monomers.
  • ethylene glycol di(meth)acrylate diethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, butylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, glycerol di(meth)acrylate, pentaerythritol triacrylate, pentaerythritol tetraacrylate, dipentaerythritol pentaacrylate, dipentaerythritol hexaacrylate, pentaerythritol di(meth)acrylate, pentaerythritol tri(meth)acrylate
  • the oxime ester compound (i.e., component C) described above may be merely used as a photopolymerization initiator, or other types of photopolymerization initiators may be further added.
  • the photopolymerization initiator, which may be further added may be selected from the following compounds:
  • halomethylated triazine derivatives for example 2-(4-methoxyphenyl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4-methoxynaphthyl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4-ethoxynaphthyl)-4,6-bis(trichloromethyl)-s-triazine, or 2-(4-ethoxycarbonylnaphthyl)-4,6-bis(trichloromethyl)-s-triazine; halomethylated oxadiazole derivatives, for example 2-trichloromethyl-5-(2′-benzofuranyl)-1,3,4-oxadiazole, 2-trichloromethyl-5-[ ⁇ -(2′-benzofuranyl)ethylenyl]-1,3,4-oxadiazole, 2-trichloromethyl-5-[ ⁇ -(2′-(
  • various additives may be further added to the photosensitive composition of this invention as needed, which include, but are not limited to, a colorant, a solvent, a sensitizer, a curing accelerator, a photo-crosslinking agent, a photosensitizer, a dispersion auxiliary agent, a filler, an adhesion promoter, an antioxidant, an ultraviolet absorbent, an anti-flocculating agent, a thermal polymerization inhibitor, a defoaming agent, a surfactant, etc.
  • a colorant e.g., a colorant, a solvent, a sensitizer, a curing accelerator, a photo-crosslinking agent, a photosensitizer, a dispersion auxiliary agent, a filler, an adhesion promoter, an antioxidant, an ultraviolet absorbent, an anti-flocculating agent, a thermal polymerization inhibitor, a defoaming agent, a surfactant, etc.
  • colorant which may be contained in the photosensitive composition of this invention, it is no particularly limited. However, it is preferred to use compounds which are classified as pigments in color index (C.I.; published by The Society of Dyers and Colourists), and colorants having the following color index (C.I.) numbers may be particularly used:
  • C.I. Pigment Yellow 1 (since C.I. Pigment Yellow is identical below, only the number is recorded for the purpose of simplification of drafting), 3, 11, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 55, 60, 61, 65, 71, 73, 74, 81, 83, 86, 93, 95, 97, 98, 99, 100, 101, 104, 106, 108, 109, 110, 113, 114, 116, 117, 119, 120, 125, 126, 127, 128, 129, 137, 138, 139, 147, 148, 150, 151, 152, 153, 154, 155, 156, 166, 167, 168, 175, 180, 185;
  • C.I. Pigment Orange 1 (since C.I. Pigment Orange is identical below, only the number is recorded for the purpose of simplification of drafting), 5, 13, 14, 16, 17, 24, 34, 36, 38, 40, 43, 46, 49, 51, 55, 59, 61, 63, 64, 71, 73;
  • C.I. Pigment Violet 1 (since C.I. Pigment Violet is identical below, only the number is recorded for the purpose of simplification of drafting), 19, 23, 29, 30, 32, 36, 37, 38, 39, 40, 50;
  • C.I. Pigment Red 1 (since C.I. Pigment Red is identical below, only the number is recorded for the purpose of simplification of drafting), 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 14, 15, 16, 17, 18, 19, 21 and 22, 23, 30, 31, 32, 37, 38, 40, 41 and 42, 48:1, 48:2, 48:3, 48:4, 49:1, 49:2, 50:1, 52:1, 53:1, 57, 57:1, 57:2, 58:2, 58:4, 60:1, 63:1, 63:2, 64:1, 81:1, 83, 88, 90:1, 97, 101, 102, 104, 105, 106, 108, 112, 113, 114, 122, 123, 144, 146, 149, 150, 151, 155, 166, 168, 170, 171, 172, 174, 175, 176, 177, 178, 179, 180, 185, 187, 188, 190, 192, 193, 194, 202, 206,
  • C.I. Pigment Blue 1 (since C.I. Pigment Blue is identical below, only the number is recorded for the purpose of simplification of drafting), 2, 15, 15:3, 15:4, 15:6, 16, 22, 60, 64, 66;
  • inorganic pigments the following may be exemplified, for example, titanium oxide, barium sulfate, calcium carbonate, zinc white, lead sulfate, massicot (yellow), zinc yellow, iron oxide red, cadmium red, ultramarine, Prussian blue, chromium oxide green, cobalt green, amber, titanium black, synthetic iron black, carbon black, etc.
  • the organic pigments and the inorganic pigments described above may be used alone respectively, may be used by mixing 2 or more kinds thereof, or the organic pigments and the inorganic pigments may be used in combination.
  • a black pigment is preferably used as the light-shielding agent.
  • a black pigment either an organic pigment or an inorganic pigment may be used, and the following may be exemplified: carbon black, titanium black (titan black), and metal oxides, complex oxides, metal sulfides, metal sulfates, or metal carbonates of copper, iron, manganese, cobalt, chromium, nickel, zinc, calcium, silver, etc.
  • carbon black having a high light-shielding property is preferably used.
  • the organic pigment described above may be suitably added as an auxiliary pigment.
  • a dispersant may be further used.
  • a polymer dispersant such as polyethyleneimine dispersant, polyurethane resin dispersant, and acrylic resin dispersant, are preferably used.
  • the acrylic resin dispersant is preferably used as a dispersant.
  • (poly)alkylene glycol monoalkyl ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol n-propyl ether, ethylene glycol mono-n-butyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol mono-n-propyl ether, diethylene glycol mono-n-butyl ether, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol mono-n-propyl ether, propylene glycol mono-n-butyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol mono-n-propyl ether, dipropylene glycol mono-n-propyl ether, dipropylene glycol monomethyl
  • thermal polymerization inhibitor used in the photosensitive composition of this invention for example, hydroquinone, hydroquinone monoethyl ether, etc., may be exemplified.
  • polysiloxane compounds As the defoaming agent, polysiloxane compounds, fluorine compounds, etc., may be used.
  • anionic surfactants As the surfactant, anionic surfactants, cationic surfactants, and nonionic surfactants may be used.
  • Another object of this invention is to provide use of the above photosensitive composition containing an oxime ester photoinitiator in a liquid crystal display apparatus, such as color filters (RGB and BM photoresists), photospacers, or ribs.
  • a liquid crystal display apparatus such as color filters (RGB and BM photoresists), photospacers, or ribs.
  • Still another object of this invention is to provide a photoresist film, a color filter film, a photospacer, and a rib prepared from the above photosensitive composition containing an oxime ester photoinitiator.
  • a contact transfer type coating apparatus such as a roll coater, a reverse coater, a rod coater, etc.
  • rotor such as a rotary coating apparatus
  • non-contact type coating apparatus such as a curtain type flowing coater
  • drying method is not particularly limited, and for example, any one of the following methods may be used: (1) a method of drying on a hot plate at 80 to 120° C., preferably 90 to 100° C. for 60 to 120 seconds; (2) a method of placing at room temperature for several hours to several days; (3) a method of removing solvent by placing in a hot-air heater or an infrared heater for tens of minutes to several hours.
  • the energy ray radiated may be ultraviolet, excimer laser etc., and the intensity may be varied according to the composition of the photosensitive composition, but is preferably 30 to 2000 mJ/cm 2 , for example;
  • the developing method is not particularly limited, and for example, a dipping method, a spraying method, etc., may be used; and developers, for example, organic substances such as monoethanolamine, diethanolamine, triethanolamine, etc., or aqueous solutions of sodium hydroxide, potassium hydroxide, sodium carbonate, ammonia, quaternary ammonium salt, etc., may be exemplified; and
  • the oxime ester photoinitiator as component (C) has a good adaptability to components (A) and (B).
  • the composition obtained has very good storage stability. It is not only suitable for normal light sources, but also has remarkably high sensitivity under the irradiation of LED light sources and laser light sources. It may be cross-linked and cured well at a very low exposure dose, and has an extremely good curing effect.
  • the film made from this composition has a smooth edge, no defects and scum, and good integrity throughout the whole pattern, and is a high-hardness resist film, and an optical filter made therefrom has high optical transparency and no light leakage.
  • BMs black matrices
  • the presence of a black pigment or dye causes the utilization effect of the light source to be extremely poor, whereas the production of BMs still may be completed at a very low exposure dose by using this composition, and the BMs produced have high light-shielding property as well as excellent precision, evenness, and durability.
  • the composition of this invention is also an excellent material for producing photospacers and ribs.
  • a photosensitive composition was formulated as follows, comprising a benzyl methacrylate/methacrylic acid/hydroxyethyl methacrylate (molar ratio 70/10/20) copolymer (Mw:10000) (50 parts by mass), dipentaerythritol hexaacrylate (25 parts by mass), a photoinitiator, and a pigment.
  • Photoinitiator Pigment (Types, Parts by mass) (Types, Parts by mass) (Types, Parts by mass)
  • Example 1 Compound No. 1, 5 Carbon black, 20
  • Example 2 Compound No. 12, 5 Carbon black, 20
  • Example 3 Compound No. 14, 5 Carbon black, 20
  • Example 4 Compound No. 24, 5 C.I. Pigment Blue-15:3, 20
  • Example 5 Compound No. 31, 5 C.I. Pigment Blue-15:3, 20
  • Example 6 Compound No. 48, 5 C.I. Pigment Blue-15:3, 20
  • Example 7 Compound No. 49, 5 C.I. Pigment Blue-15:3, 20
  • Example 8 Compound No. 54, 5 C.I.
  • the photosensitive composition was formulated according to the formulation shown in Table 1, and was dissolved in 100 parts by mass of a solvent propylene glycol monomethyl ether acetate (PGMEA) to form a liquid-state composition.
  • PGMEA solvent propylene glycol monomethyl ether acetate
  • the liquid-state composition was coated on a glass substrate by using a spin coater, and the solvent was removed by drying at 90° C. for 5 min to form a coating film having a film thickness of 1.5 ⁇ m; and in order to obtain the coating film having the thickness described above, the coating process may be completed by one time or multiple times.
  • the substrate on which the coating film was formed was cooled to room temperature, a mask plate was attached thereon, and the coating film was exposed with a 395 nm LED light source.
  • the minimum exposure amount of the irradiated region having a residual film rate of 90% or more after development in the step of exposure was evaluated as the exposure demand A smaller exposure demand represents a higher sensitivity.
  • the pattern on the substrate was observed using a scanning electron microscope (SEM) to evaluate the developability and the pattern integrity.
  • SEM scanning electron microscope
  • the developability was evaluated according to the following criteria:
  • the pattern integrity was evaluated according to the following criteria:
  • compositions of Examples 1-8 have extremely excellent storage stability in solution systems and small exposure demand, and color filter photoresists produced therefrom have good developability and pattern integrity. Each performance is superior to that of Comparative Examples 1-3.
  • the exposure doses of the compositions of Examples 1-8 under the irradiation of LED dot lamp light sources are all less than 50 mJ/cm 2 , which is far lower than those of Comparative Examples 1-3, exhibiting extremely excellent photosensitivity. This provides a good promotional effect on generalization and application of energy-saving and environment-friendly LED dot light sources in the technical field of photocuring.
  • the photosensitive composition containing an oxime ester photoinitiator of this invention exhibits a very excellent application performance and has a wide prospect for application.

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JP2017523465A (ja) 2017-08-17
JP6510028B2 (ja) 2019-05-08
CN104076606B (zh) 2019-12-03
CN104076606A (zh) 2014-10-01
KR20170031717A (ko) 2017-03-21
WO2016008384A1 (zh) 2016-01-21

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